Holiday rentals in Lakeland Highlands

Private Studio Suite

🧳 Perfect for a solo traveler or couple looking to visit the peaceful city of Lakeland. 📍Located about 40 minutes from Tampa and an hour from Orlando, in the family friendly area of Lakeland Highlands. - There’s nearby trails, grocery stores, convenience stores and eateries. - Polk Parkway is less then 10 minutes away, it’s the quickest route to get to i4. 🏠 The suite includes a private entrance with full bathroom and backyard area. 🚗 Free Parking Space(s) 👐🏽 Flexible & Contactless Entry

Christina Casa - a South Lakeland Getaway

Welcome to Christina Casa, your ultimate vacation retreat! Nestled in a quiet South Lakeland Neighborhood, this charming 3-bedroom has 2 full baths. The fully stocked kitchen invites culinary adventures, while the cozy living room offers a plethora of games and books for endless entertainment. Step outside to the inviting patio area, complete with a grill for delightful outdoor dining experiences. Embrace relaxation and adventure at Christina Casa, where making memories await! Come be our guest!

Updated home with heated & screened in pool

Recently renovated from top to bottom. The bedrooms have a king, queen, and bunk beds. Have a movie night with the 4k projector on the 125 inch screen and a Dolby Atmos soundbar. Cool off and away from bugs in the screened in heated/cooled pool that goes from 3 to 6 feet deep, then relax on the patio furniture. Newly landscaped spacious back yard. Quiet neighborhood so absolutely no parties. Centrally located between Tampa & Orlando. Theme parks, beaches and so much more within an hour or two.

The Woodsy Weekender

Take it easy at this unique and tranquil getaway in the woods. Wake up in one of our cozy queen or full sized beds, and enjoy coffee and hot chocolate on the 2nd story deck. 10 minutes from downtown Lakeland, spend your day walking our beautiful lakes and eating at our foodie hotspots. End your day back the at Woodsy Weekender making dinner in our full kitchen and sipping wine on the screened in back porch swings watching the sunset. The perfect little "Safe Haven" cabin for all occasions.

The Highland House • Cozy 3BR • Fireplace • Patio

Stylish and spacious, this South Lakeland retreat is the perfect home base for your stay. Enjoy a beautifully updated interior with an open-concept layout, modern kitchen, and cozy living space for relaxing or gathering. With comfortable bedrooms, a large dining area, and plenty of room to unwind, it’s ideal for families, groups, or work trips. Features a screened patio, fenced yard, and keyless entry, all in a quiet neighborhood close to shopping, dining, and local attractions.

Casa Planta Cozy Tropical Oasis Pool View Suite

Casa Planta is a garden-inspired oasis where nature & relaxation meet. Our tropical landscape is currently in a seasonal restoration phase due to extreme winter freezes, w/ an evolving garden setting. Enjoy a peaceful walk to your private entrance & unwind poolside in your 2BR/1BA suite. The pool and interior remain exactly as pictured—private, comfy, & serene. The guest suite is attached to the main house but completely blocked off from it.

Charming Guesthouse

Escape to a beautifully styled South Lakeland retreat, loved by guests for its comfort, peaceful setting, and convenient location. Settle into a cozy, thoughtfully designed space with fast WiFi, relaxing touches, and a quiet neighborhood feel. Spend your days exploring nearby lakes, dining, shopping, and Central Florida attractions, then return home to unwind, recharge, and enjoy a stay that feels effortless.

Heart of South Lakeland in adorable neighborhood!

In the heart of South Lakeland, in one of the most sought out locations. Easy access to a variety of restaurants, shopping and minutes away from the Polk Parkway and South Florida Ave. Whether your destination is here in Lakeland, to the beach, or off to see Mickey, our goal is to make you feel at home! The home features a newly remodeled kitchen, a smart tv, memory foam mattresses, and all the coffee!

Intimate and peaceful stay

Rest in this intimate and serene room, perfect for two guests. It has a bedroom with a king-size bed, a full bathroom, and an equipped kitchen. The white design conveys calm and freshness. Enjoy the private patio with swing and outdoor table. Start the day with coffee under the sky or relax in the afternoon on the swing. Ideal for couples or solo travelers seeking privacy and tranquility.

Lakeland Highlands Oasis - 3BR Heated Pool Home

* No Pets* Welcome to the Lakeland Highlands Oasis! A 3-bedroom, 2-bath pool home is tucked into a quiet street in South Lakeland, offering the perfect blend of space, location, and peace and quiet. This thoughtfully curated home is designed for comfort—with a spacious backyard,a private pool, and inviting interiors that feel like home. No bbq grill.

Discount + Pet Friendly + Fence Yard + Internet

Book now! ➤ Minutes from Downtown ➤ Fully fenced backyard for pets ➤ Free parking for cars, trailers, or boats ➤ 2 Queen beds - Sleeps 4 ➤ 55" Smart TV ➤ Internet - Fiber Fast Wi-Fi ➤ Coffee Included! ➤ Prime location near I-4, Lake Hollingsworth, & dining Have questions? Message us—we're here to help!

Karen's Cottage

Enjoy a stylish experience at this centrally-located place. Private entrance and fenced back yard. Between Tampa and Orlando so there’s a lot of things to do. Lakeland has a wonderful and thriving community.